Find Romantic Hotels in Chester, VT

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Check availability on Chester Romantic Hotels

Top Chester Romantic Hotels

Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1004)
"Hotel itself clean and nice but surrounding area has homeless people, or seems a little sketchy, which made us a little nervous walking around town "
The price is SAR 555
SAR 602 total
includes taxes & fees
24 Jul - 25 Jul
Courtyard by Marriott Keene Downtown
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 831
SAR 1,020 total
includes taxes & fees
16 Jul - 17 Jul
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is SAR 731
SAR 1,210 total
includes taxes & fees
14 Jul - 15 Jul
Family Friendly Hilltop House In Putney Vermont
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is SAR 1,129
SAR 1,225 total
includes taxes & fees
15 Jul - 16 Jul
Chesterfield Inn
Riverside Hotel, Ascend Hotel Collection
Sundeck

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (575)
"Great hotel experience from the moment we checked in. The service was excellent, hotel and rooms were so clean, and the sleep number bed was the best! It's a gem of a hotel! "
The price is SAR 571
SAR 619 total
includes taxes & fees
21 Jul - 22 Jul
Riverside Hotel, Ascend Hotel Collection
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is SAR 995
SAR 1,094 total
includes taxes & fees
15 Jul - 16 Jul
Inn on Putney Road
The Inn at Weathersfield
Interior

The Inn at Weathersfield

4.0 star property
10.0 out of 10, Exceptional, (63)
"Great Inn."
The Inn at Weathersfield
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is SAR 514
SAR 560 total
includes taxes & fees
27 Jul - 28 Jul
Colonel Williams Inn
Pointe at Castle Hill Resort
Indoor pool

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (851)
"Staff was excellent "
The price is SAR 539
SAR 614 total
includes taxes & fees
17 Jul - 18 Jul
Pointe at Castle Hill Resort
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (100)
"Great location and house was very nice."
The price is SAR 656
SAR 1,449 total
includes taxes & fees
15 Jul - 16 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need a romantic vacation, we'd like to help you plan for it. Couples choose Chester for its coffeehouses and restaurants. During your trip, you might consider a visit to DaVallia Art & Accents or Bonnie's Bundles Dolls while you're exploring Chester with your significant other. Whether you'd like to sip a glass of champagne or get a couples' massage, you'll be sure to find accommodation in Chester to make for the perfect couples' getaway.
What's the best place to stay for a romantic getaway to Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a fitness center.
How many romantic hotels will we find in Chester?
Expedia has 5 romantic Chester hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Chester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Chester has to offer. Couples looking for a little of everything will enjoy Chester for its coffeehouses, restaurants, and skiing. You might consider a stop at DaVallia Art & Accents or Bonnie's Bundles Dolls while you're out and about.
What's the best way to get to Chester and around town during my romantic getaway?
These transportation options in Chester might help your romantic trip go off without a hitch: The closest major airport is Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.